According to Chris Ainsworth of the gaming blog Driph, the Awesome Face was part of a series of emoticons designed and illustrated for the Pokemon-related web forum Pokemopolis. He claims to have contacted the creator of the image, and published the following correspondence:
I drew the icon years ago as part of an emoticon set he wanted for their new forum software, and I think he showed you all the other ones that were designed along with it. I』m not really sure what exactly I wanted it to represent but I think the 『ridiculous childish glee』 that it now signifies is probably close!
I』m also a member at Something Awful and the first time I saw it posted I did a double take… I even remember my mind racing as to why and HOW someone had picked up a crappy lil』 icon off a tiny website, and I』m still not sure to this day… I assume a Pokemopolis member posted it on 4Chan. At that point I thought its posting would be a one time thing, but then I saw it more and more. It got to the point where I couldn』t read SA because everytime I saw it I』d just be completely freaked out, and naturally I came to hate it! I hoped every day that it would become bannable to post it, but the next best thing was replacing the VBCode. I also posted inBYOB in a thread Whalley made saying that I had made the icon originally, trying to get him to divulge wherehe had gotten it from. Most of SA assumed it was a 『BYOB thing』 which was probably good because they』d probably want to lynch me if they actually knew where it was from.
I never expected it to become such a widespread meme, and I can』t say I even understand why its popular or why people want to make bag pins of it (Sure wish I could get some commission for the design though haha). It still weirds me out when I see webcomics use it though I』ve grown used to it now, sometimes I even tell nerdy neckbeard types that my dirty secret is psst I drew THAT smiley, which makes them say 「MOAR!」 or whatever is cool on 4Chan this week.
Though just for clarity sake my excuse for being on a Pokemon site in the first place was that I was young and stupid. But that』s the price of Internet fame!